In 2013, countless things went right for Cherington's team. The roster blended together, stayed healthy and was fully on board with manager John Farrell's message on a daily basis.
It's hard to create that type of dynamic two years in a row, which explains why there has been no repeat champion since the Yankees of 1998-2000.
Cherington was with Boston the last two times the team tried to repeat, but each time, the club came up a little short.
"I obviously wasn't in this chair [in 2007], and in '04, I wasn't really working that closely at the Major League level," said Cherington. "But I remember at the time, one of the things we discussed and [former GM] Theo Epstein felt strongly about is that if you try to replicate exactly what you have this year, it's probably not going to work quite the same."
So in the coming days, weeks and perhaps even months, Cherington and his staff will bunker down and figure out exactly what to tinker with.
Much of it will have to do with which free agents are retained and which move on.
The Red Sox could get some answers to that question as early as Monday, when the three free agents (Jacoby Ellsbury, Mike Napoli and Stephen Drew ) they extended qualifying offers to must accept or decline.
Ellsbury is sure to decline. But if Napoli or Drew accept, it would mean they will return on a one-year, $14.1 million commitment for next season.
Here is a closer look at the offseason that awaits the Sox.
Arbitration-eligible: RHP Andrew Bailey , LHP Franklin Morales , LHP Andrew Miller , RHP Junichi Tazawa , 1B/OF Mike Carp
Free agents: OF Ellsbury, SS Drew, 1B Napoli, C Jarrod Saltalamacchia , RHP Joel Hanrahan
Here is a look at how the club shapes up, position by position.
Rotation: This is perhaps the most stable area of the club going into the winter. The Red Sox have six established starters under contract for next season in Jon Lester, Clay Buchholz, John Lackey, Jake Peavy, Felix Doubront and Ryan Dempster.
Don't be so sure Cherington will move one of those starters this offseason. Instead, he will likely bring the six to Spring Training and take inventory then, and make sure everyone is healthy.
"We think it's a position of strength," Cherington said. "We have the six guys that you referred to, plus we think we have the younger starting-pitching candidates who have either gotten a little taste of it or are on their way. So relative to past years, we think it's an area of strength and depth. And yeah, we could certainly envision a scenario where everyone that's currently under contract will be in Fort Myers. And in fact, at this point, that's what I would expect. We'll see what the offseason brings."
Bullpen: At the key spots, the Red Sox could look very similar. Koji Uehara will again be the closer, though it's important to be mindful of the fact he'll be 39 next season. Tazawa and Craig Breslow will be key components to the setup staff again. Lefty Miller, who dominated in the first half until breaking his left foot, should be back.
Bailey, whose first two seasons in Boston have been filled with frustrating injuries, is all but sure to be non-tendered, but the Red Sox could bring him back at a discounted rate. Brandon Workman is a bright young prospect who proved he's capable of helping as a starter or reliever.
Catcher: The Red Sox at least know who their backup is. The highly respected David Ross will be back for a second season in that capacity. There's a chance Ross will again form a tandem with Saltalamacchia, whose strong regular season has been overshadowed a bit by his quiet postseason. Saltalamacchia didn't get a qualifying offer, so he will gauge the market, which should include Boston.
The Red Sox know the obvious advantage in bringing Saltalamacchia back. He knows the pitching staff and provides power, particularly from the left side. Brian McCann, who teamed with Ross in Atlanta, is easily the most intriguing free agent at the position. Would Boston be willing to meet his price tag?
First base: Napoli is Option A. Though there was a long slump in the middle of the season, the right-handed-hitting slugger was there when it counted. He also played stellar defense at first base, something that wasn't expected when he converted from catcher. Napoli had obvious comfort playing in Boston and liked the spotlight. But the Red Sox would only give him one year last winter because of the hip condition they detected during his physical. Whether or not Napoli comes back could depend on if the Sox will give him a multiyear deal now that they've had the chance to monitor him on a daily basis.
As for in-house candidates should Napoli leave, the Red Sox might at least consider Carp, who clearly made the most of his limited playing time last season. Daniel Nava can play first also, but he remains targeted for the outfield.
Second base: This position should be set through 2021, the final year the Red Sox have contractual control over star second baseman Dustin Pedroia. In 2013, Pedroia once again proved that he was an elite performer who was perfectly willing to play through injury. Pedroia is getting his left thumb repaired next week, and he hopes that he'll get some power back next season. The Sox didn't really have a backup second baseman down the stretch this season, and when Pedroia's healthy, they don't really need one.
Shortstop: Here's where things get interesting. Because the Red Sox made Drew a qualifying offer, they are assured of a Draft pick if he signs elsewhere. But if Drew accepts, Boston will pay a fairly steep price ($14.1 million) considering his offensive inconsistency. However, Drew is a terrific defender, and the Red Sox aren't opposed to high base salaries when they are part of a short-term commitment.
If Drew doesn't return, top prospect Xander Bogaerts could get a chance to win the job at his natural position. Bogaerts played mostly third base at the Major League level in 2013. His bat is a known commodity, but the jury is still out a bit on how good Bogaerts can be defensively at short.
Third base: If Drew comes back, the Red Sox could have two of their most promising young players (Will Middlebrooks and Bogaerts) in an old-fashioned position battle to win the hot corner. Bogaerts would seem like the front-runner, given the way he performed under fire in the postseason. However, Middlebrooks struggled mightily in 2013, his sophomore season, and that could be a cautionary tale for Bogaerts.
Though there might be some speculation that Middlebrooks could be traded, Boston generally doesn't trade players when their value is low. In other words, the Sox might be more inclined to bring him back and allow him to increase his potential worth to other teams.
Outfield: The corners appear set. Shane Victorino will patrol right field, and assuming he regains his health this winter, he will likely return to switch-hitting next year. Victorino was almost exclusively a right-handed batter the final three months of the season. Moving from center to right, Victorino brought home his fourth career Gold Glove Award. It remains to be seen who will play alongside him in center. Ellsbury could well sign elsewhere, and Jackie Bradley Jr., who is comparable defensively, could get a shot in center.
Farrell loved his left-field platoon of Nava and Jonny Gomes, and he expects to deploy it again in 2014. Don't read anything into the fact Gomes essentially took over the job in the postseason. Farrell has said numerous times he was playing the hot hand. Over the course of the regular season, he very much likes the combination which will most often have Nava in there against righties and Gomes playing against southpaws.
Designated hitter: Considering all he has done in his time with the Red Sox, it's hard to believe David Ortiz could have increased his legend this October. But that's exactly what he did, coming up with one big hit after another and taking home the Most Valuable Player Award in the World Series. Ortiz will be 38 in 2014, but the Red Sox hope he has at least one more big year left in him.